CA1128854A - Fungicidal formulations - Google Patents
Fungicidal formulationsInfo
- Publication number
- CA1128854A CA1128854A CA324,339A CA324339A CA1128854A CA 1128854 A CA1128854 A CA 1128854A CA 324339 A CA324339 A CA 324339A CA 1128854 A CA1128854 A CA 1128854A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- fungicidal
- weight
- formulations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT
Fungicidal formulations are described which comprises as a first fungicidally active ingredient a triazole or pyrimidine of formula :- or I(a) I(b) where X is chlorine or fluorine and as a second fungicidally active ingredient a compound of formula :
or
Fungicidal formulations are described which comprises as a first fungicidally active ingredient a triazole or pyrimidine of formula :- or I(a) I(b) where X is chlorine or fluorine and as a second fungicidally active ingredient a compound of formula :
or
Description
This invention relates to fungicidal formulations and to methods of treating fungal infections of cultivated plants.
According to one aspect of the present invention, there is provided a fungicidal formulation comprising as a first~fungicidally active ingredie t a triazole or pyrimidine of formula :-r'lD ' ~ ~\`Cl Cl ~ O-CH-CO-C(CH3)3 ~ ~ C OH
I(a) ~ l(b) . X
where X is chlor1ne or fluorine ? and as a second fungicidally active - ingrçdient a compound of formula : - .
; 20 CIH3 0 ll N or C2H5NH~NHCCCN
\ CO - R NOCH3 .
II(a) II(b) 25where R is fur-2-yl or -CH20CH3, . associated with one or more inert, non-phytotoxic carrier(s) therefor.
A11 of the aforementioned compounds are known compounds and may be prepared by methods well-defined in the literature. The triazole of formula I(a) is described in U.S. Patent Specification No. 3,912,752, the pyrimidines of formula I(b) in U.K. Patent Specification No. 1,218,623, the alanine derivatives of formula II(a) in U.K. Patent Specification ., _~
.
No. 1,448,810 and 8elgian Patent Specification No. 827,57i and the urea of formula II(b) in U.K. Patent Specification No. 1,470,740.
~ The combinations of active ingredients defined in the above formul-; ation are novel and have been Found to be surprisingly effective in controlling or combatting fungal infections of cultivated plants. They are ; of value in the treatment of a wide range of cultivate~ crops susceptible to fungal attack, such as for example cereals an~ beans, and in particular crops susceptible to powdery and downy mi1dew, as well as late blight, i.e. crops such as grapes, cucurbits and tobacco susceptible to attack by microorganisms of nomycestes an~ Erysiphales sp~cies According to a second aspect of the invention, there is provided a method of treating fungal infections of plants especially grapes which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as deFined above.
In the aforesaid method, the formulation can be applied by foliar .. .. .. __ . .. . . ., . .. .
application or soil drench, depending on the crop being treated, at any time after crop emergence until harvesting takes place. The amount and frequency of application will be determined by the severity or expected
According to one aspect of the present invention, there is provided a fungicidal formulation comprising as a first~fungicidally active ingredie t a triazole or pyrimidine of formula :-r'lD ' ~ ~\`Cl Cl ~ O-CH-CO-C(CH3)3 ~ ~ C OH
I(a) ~ l(b) . X
where X is chlor1ne or fluorine ? and as a second fungicidally active - ingrçdient a compound of formula : - .
; 20 CIH3 0 ll N or C2H5NH~NHCCCN
\ CO - R NOCH3 .
II(a) II(b) 25where R is fur-2-yl or -CH20CH3, . associated with one or more inert, non-phytotoxic carrier(s) therefor.
A11 of the aforementioned compounds are known compounds and may be prepared by methods well-defined in the literature. The triazole of formula I(a) is described in U.S. Patent Specification No. 3,912,752, the pyrimidines of formula I(b) in U.K. Patent Specification No. 1,218,623, the alanine derivatives of formula II(a) in U.K. Patent Specification ., _~
.
No. 1,448,810 and 8elgian Patent Specification No. 827,57i and the urea of formula II(b) in U.K. Patent Specification No. 1,470,740.
~ The combinations of active ingredients defined in the above formul-; ation are novel and have been Found to be surprisingly effective in controlling or combatting fungal infections of cultivated plants. They are ; of value in the treatment of a wide range of cultivate~ crops susceptible to fungal attack, such as for example cereals an~ beans, and in particular crops susceptible to powdery and downy mi1dew, as well as late blight, i.e. crops such as grapes, cucurbits and tobacco susceptible to attack by microorganisms of nomycestes an~ Erysiphales sp~cies According to a second aspect of the invention, there is provided a method of treating fungal infections of plants especially grapes which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as deFined above.
In the aforesaid method, the formulation can be applied by foliar .. .. .. __ . .. . . ., . .. .
application or soil drench, depending on the crop being treated, at any time after crop emergence until harvesting takes place. The amount and frequency of application will be determined by the severity or expected
2~ severity of the fungal disease and, as is well known to those skilled in the art, by the age and condition of the crop. However, it is a feature of the invention and a particular advantage obtainçd therefrom that a reduced frequency of treatment, for example only once evèry 2 to 3 weeks to control ; grape milde~l infections, may be effectively employed,thus achieving a valuable reduction in labour costs.
I The preferred pyrimidine for use in foliar application for instance ¦, in grape treatment is that in which X is chlorine. However, when application ¦~ of the combination of the invention is to be effected by means of a soil ¦l drench it has been found that the pyrimidine of formula I in ~hich X is i fluorine is particularly efficacious.
As stated above, formulations of this invention are applied by foliar application or by soil drench. In soil drenches, the compounds Of formula I (a) and I (b) are preferably applied in an amount of from 50 to 500g per hectare, whereas the compounds of formula II(a) are preferably applied in amounts of from 500 to 3000g per hectare. Thus the ratio of compounds of formula I to compounds of formula II(a) in such formulations may preferably range from 1:1 to 1:60 by weight.
When foliar application is utilised the compound of formula I(a) is preferably applied at a rate of from 10 to 500g per hectare, whereas the compounds of formula I(b) are preferably applied at a rate of from 10 to lOOg per hectare.
The compound of formula II(a) is preferably applied at a rate of from 100 to 2,500g per hectare. In such circumstances, the compound of formula II(b) is preferably applied at a rate of from 50 to 500g/hectare. Accordingly, the ratio of compounds of formula I to compounds of formula II in formulations applied by foliar application is preferably from 5:1 to 1:250 by weight.
The formula II(b) compound is preferably used in com-bination with a further fungicide, such as for example zineb or ; mancozeb, and as specified in U.K. Patent Specification No.
1,470,740. It should be noted that such further fungicides are used at approximately half their normal rate and that the compound of formula II(b) is not compatible with compounds which increase alkalinity.
In order to simplify manufacture, storage and trans-port, the combinations of the formulae I and II compounds will be normally produced in concentrate from intended for dilution in water to the degree necessary to enable the above mentioned application rates to be easily achieved. Such concentrated formulations may contain from 0.5 to 90%, preferably 5 to 90%, 7~
. ~
~1~8~3S~
- 4a-by weight of active ingredients associated with one or more inert non-phytotoxic carrier(s~ therefor. Such formulations will usually be in the form of a wettable powder or dust, aqueous suspension, emulsifiable concentrate or granules.
The concentrate formulations are intended for appropriate ~;,,, i .. ..
385~
dilution with water prior to use. This formation of an aqueous dispersion can be carried out in conventional spray tanks suitable for the purpose.
It is to be clearly understood that the diluted formulations so produced are formulations in accordance with the invention in which one or all of the inert non-phytotoxic carrier(s) is water.
Wettable powders or dusts comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays 9 the diatomaceous earths, kaolins, micas, talcs and purified silicates.
Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates~ the alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenol. Illustrative of wettable powders falling within the scope of the invention are those having the following composition :
Wettab1`e Powders ~ by weight Formula I compound l to lO
Formula II compound 5 to 60 Surfactant(s) 0 to lO
Dispersing Agent 0 to lO
Anticaking agent 0 to 15 Inert carrier(s) to lO0 j The following non-limitative Examples will serve to further illustrate i the invention.
The compound of formula I in which Y is chlorine is known as fenarimol, whilst the related compound in which X is fluorine is kno~.~/n as nuarimol.
I Simil3rly, the compound of formula I(a) is known as triadimefon. In the 3û Examples below the compound of formula II(a) in which R is fur-2-yl is represented by the letter "A", the formula II(a) compound in which ;l -5-1, :
~p~
R is -CH20CH3 by "B" and the formula II(b) compound by "C"
EXAMPLES l to lO
The following wettable powders were prepared :- ¦
(l) ~O by weight Compound A 25 Fenarimol 5.0 Sodium lauryl sulphate 4.0 Sodium lignin sulphonate 3.0 Precipitated silica 8.0 - Kaolin clay to lOO.O
(2) ~0~ by weight Compound A 50.0 Nuarimol 2.5 Sodium dioctyl sulphosuccinate 5.0 Sulphonated lign1n 2.0 Diatomaceous earth to lOO.O
: ~ . ~ , 2û (3) ~O' by weiqht Compound 8 40.0 Fenarimol 4.0 Ethoxylated alkyl phenol 3.0 Sodium lignin sulphonate 5.0 I Hydrated sodium silicoaluminate 4.0 I Talc to lOO.O
~l 1l -6-1' .
1~2.~
ll (4) O by weight ~uarimol 2.0 Compound B 40.û
Sodium alkylnaphthalene sulphonate a . o Silica 3.0 Kaolin to lO0.0 (5) ~ by weight Compound C 36.0 Fenarimol 6.0 Sodium alkyl ether sulphate 4.0 Sodium lignin sulphonate 3.0 Silica 7.0 . Attapulgite to 100~0 (6) . O by weight Compound C 6.0 F~narimol l.0 Zineb 50.0 Sodium salt of condensed naphthalene sulphonic acids 3.0 Sodium lignin sulphonate 4.0 Hydrated sodium silicoaluminate 8.0 Montmorillonite to lO0.0 (7) O by weight Compound C 3.0 Fenarimol 0-5 Mancozeb 36.0 Sulphite lye powder 2.0 I Sodium laurylsulphate 5.0 I Silica 6.n Kaolin to 100.0 _7_ i ~ s~
(8) ,~ by weight Compound A 40.0 Triadimefon lO.0 Ethoxylated nonyl phenol 5.0 Sodium lignin sulphonate 2.0 Silica 4.0 Talc to lO0.0 (9) ~ by weight Compound B 50.0 Triadimefon lO.0 Sodium lauryl sulphate 2.0 Sodium salt of condensed naphthalene 4.0 Sulphonic acids Precipitated silica 6.0 Kaolin to lO0.0 (lO) ~ ~ by weight Compound C 30.0 Triadimefon lO.0 Sodium dioctyl sulphosuccinate 3.0 Sulphonated lignin 4.0 Hydrated sodium silicoaluminate 8.0 Attapulgite to lO0.0 In each of the above Examples, the active ingredients were carefully ¦
I blended with the specified excipients in conventional mlxing equipment.
¦ The blend was then further milled in a fluid energv mill to a size range of from l to lO microns and finally the mixture was reblended and deaerated prior to being packaged.
Il ~
I~, I
~ 35~ 1 . ,, The formulations described in Examples l,3 and 5 to lO are intendod for use in foliar application whereas the formulations of Examples 2 and 4 are of value as soil drenches.
E~AMPLE ll The following Example illustrates the typical synergistic activity to be observed when combinations of the inventions are employed For control of fungal organisms.
Solutions of fenarimol in water were prepared at a concentration of lû and 20 parts per million and solutions of compound 8 at a concentration of 50 andlOO parts per million. They were applied separately and together to ll day old Pinto bean plants. . A single treatment consisted in spraying 3 pats, each pot containing two plants.
When the plants had dried they were inoculated with a suspension of spores of bean leaf rust and incubated for 48 hours in a cool moist chamber. ¦
The percentage control of the disease was then noted as follows :
_ . -FENARIMOL CaMPOUND B Percentage control by (concentrate (percentage (concentrate (percentage combination of p-p-m) disease p-p-m) disease fenarimol and control) control) compound 8 ~ _ _ _ lOO 29 85 77 lOO 29 96 . I . I
~5 I
I 'I
I i .
_9_ Il ~LlZ8~
When analysed by the well-known "Calby equation" ~see ~leeds ? 15, 20-22 (1967) the above results clearly showed that under the conditions of the test,this mixture of the invention demonstrated synergism.
~ ~ I
I The preferred pyrimidine for use in foliar application for instance ¦, in grape treatment is that in which X is chlorine. However, when application ¦~ of the combination of the invention is to be effected by means of a soil ¦l drench it has been found that the pyrimidine of formula I in ~hich X is i fluorine is particularly efficacious.
As stated above, formulations of this invention are applied by foliar application or by soil drench. In soil drenches, the compounds Of formula I (a) and I (b) are preferably applied in an amount of from 50 to 500g per hectare, whereas the compounds of formula II(a) are preferably applied in amounts of from 500 to 3000g per hectare. Thus the ratio of compounds of formula I to compounds of formula II(a) in such formulations may preferably range from 1:1 to 1:60 by weight.
When foliar application is utilised the compound of formula I(a) is preferably applied at a rate of from 10 to 500g per hectare, whereas the compounds of formula I(b) are preferably applied at a rate of from 10 to lOOg per hectare.
The compound of formula II(a) is preferably applied at a rate of from 100 to 2,500g per hectare. In such circumstances, the compound of formula II(b) is preferably applied at a rate of from 50 to 500g/hectare. Accordingly, the ratio of compounds of formula I to compounds of formula II in formulations applied by foliar application is preferably from 5:1 to 1:250 by weight.
The formula II(b) compound is preferably used in com-bination with a further fungicide, such as for example zineb or ; mancozeb, and as specified in U.K. Patent Specification No.
1,470,740. It should be noted that such further fungicides are used at approximately half their normal rate and that the compound of formula II(b) is not compatible with compounds which increase alkalinity.
In order to simplify manufacture, storage and trans-port, the combinations of the formulae I and II compounds will be normally produced in concentrate from intended for dilution in water to the degree necessary to enable the above mentioned application rates to be easily achieved. Such concentrated formulations may contain from 0.5 to 90%, preferably 5 to 90%, 7~
. ~
~1~8~3S~
- 4a-by weight of active ingredients associated with one or more inert non-phytotoxic carrier(s~ therefor. Such formulations will usually be in the form of a wettable powder or dust, aqueous suspension, emulsifiable concentrate or granules.
The concentrate formulations are intended for appropriate ~;,,, i .. ..
385~
dilution with water prior to use. This formation of an aqueous dispersion can be carried out in conventional spray tanks suitable for the purpose.
It is to be clearly understood that the diluted formulations so produced are formulations in accordance with the invention in which one or all of the inert non-phytotoxic carrier(s) is water.
Wettable powders or dusts comprise an intimate mixture of the active ingredients, one or more inert carriers and appropriate surfactants. The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays 9 the diatomaceous earths, kaolins, micas, talcs and purified silicates.
Effective surfactants may be found among the sulfonated lignins, the naphthalene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates~ the alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenol. Illustrative of wettable powders falling within the scope of the invention are those having the following composition :
Wettab1`e Powders ~ by weight Formula I compound l to lO
Formula II compound 5 to 60 Surfactant(s) 0 to lO
Dispersing Agent 0 to lO
Anticaking agent 0 to 15 Inert carrier(s) to lO0 j The following non-limitative Examples will serve to further illustrate i the invention.
The compound of formula I in which Y is chlorine is known as fenarimol, whilst the related compound in which X is fluorine is kno~.~/n as nuarimol.
I Simil3rly, the compound of formula I(a) is known as triadimefon. In the 3û Examples below the compound of formula II(a) in which R is fur-2-yl is represented by the letter "A", the formula II(a) compound in which ;l -5-1, :
~p~
R is -CH20CH3 by "B" and the formula II(b) compound by "C"
EXAMPLES l to lO
The following wettable powders were prepared :- ¦
(l) ~O by weight Compound A 25 Fenarimol 5.0 Sodium lauryl sulphate 4.0 Sodium lignin sulphonate 3.0 Precipitated silica 8.0 - Kaolin clay to lOO.O
(2) ~0~ by weight Compound A 50.0 Nuarimol 2.5 Sodium dioctyl sulphosuccinate 5.0 Sulphonated lign1n 2.0 Diatomaceous earth to lOO.O
: ~ . ~ , 2û (3) ~O' by weiqht Compound 8 40.0 Fenarimol 4.0 Ethoxylated alkyl phenol 3.0 Sodium lignin sulphonate 5.0 I Hydrated sodium silicoaluminate 4.0 I Talc to lOO.O
~l 1l -6-1' .
1~2.~
ll (4) O by weight ~uarimol 2.0 Compound B 40.û
Sodium alkylnaphthalene sulphonate a . o Silica 3.0 Kaolin to lO0.0 (5) ~ by weight Compound C 36.0 Fenarimol 6.0 Sodium alkyl ether sulphate 4.0 Sodium lignin sulphonate 3.0 Silica 7.0 . Attapulgite to 100~0 (6) . O by weight Compound C 6.0 F~narimol l.0 Zineb 50.0 Sodium salt of condensed naphthalene sulphonic acids 3.0 Sodium lignin sulphonate 4.0 Hydrated sodium silicoaluminate 8.0 Montmorillonite to lO0.0 (7) O by weight Compound C 3.0 Fenarimol 0-5 Mancozeb 36.0 Sulphite lye powder 2.0 I Sodium laurylsulphate 5.0 I Silica 6.n Kaolin to 100.0 _7_ i ~ s~
(8) ,~ by weight Compound A 40.0 Triadimefon lO.0 Ethoxylated nonyl phenol 5.0 Sodium lignin sulphonate 2.0 Silica 4.0 Talc to lO0.0 (9) ~ by weight Compound B 50.0 Triadimefon lO.0 Sodium lauryl sulphate 2.0 Sodium salt of condensed naphthalene 4.0 Sulphonic acids Precipitated silica 6.0 Kaolin to lO0.0 (lO) ~ ~ by weight Compound C 30.0 Triadimefon lO.0 Sodium dioctyl sulphosuccinate 3.0 Sulphonated lignin 4.0 Hydrated sodium silicoaluminate 8.0 Attapulgite to lO0.0 In each of the above Examples, the active ingredients were carefully ¦
I blended with the specified excipients in conventional mlxing equipment.
¦ The blend was then further milled in a fluid energv mill to a size range of from l to lO microns and finally the mixture was reblended and deaerated prior to being packaged.
Il ~
I~, I
~ 35~ 1 . ,, The formulations described in Examples l,3 and 5 to lO are intendod for use in foliar application whereas the formulations of Examples 2 and 4 are of value as soil drenches.
E~AMPLE ll The following Example illustrates the typical synergistic activity to be observed when combinations of the inventions are employed For control of fungal organisms.
Solutions of fenarimol in water were prepared at a concentration of lû and 20 parts per million and solutions of compound 8 at a concentration of 50 andlOO parts per million. They were applied separately and together to ll day old Pinto bean plants. . A single treatment consisted in spraying 3 pats, each pot containing two plants.
When the plants had dried they were inoculated with a suspension of spores of bean leaf rust and incubated for 48 hours in a cool moist chamber. ¦
The percentage control of the disease was then noted as follows :
_ . -FENARIMOL CaMPOUND B Percentage control by (concentrate (percentage (concentrate (percentage combination of p-p-m) disease p-p-m) disease fenarimol and control) control) compound 8 ~ _ _ _ lOO 29 85 77 lOO 29 96 . I . I
~5 I
I 'I
I i .
_9_ Il ~LlZ8~
When analysed by the well-known "Calby equation" ~see ~leeds ? 15, 20-22 (1967) the above results clearly showed that under the conditions of the test,this mixture of the invention demonstrated synergism.
~ ~ I
3~
11 ~
, ~,
11 ~
, ~,
Claims (9)
1. A fungicidal formulation comprising as a first fungicidally active ingredient a triazole or pyrimidine of formula :- or I(a) I(b) where X is chlorine or fluorine, and as a second fungicidally active ingredient a compound of formula :
or II(a) II(b) where R is fur-2-yl or -CH2OCH3, associated with one or more inert, non-phytotoxic carrier(s) therefor.
or II(a) II(b) where R is fur-2-yl or -CH2OCH3, associated with one or more inert, non-phytotoxic carrier(s) therefor.
2. A fungicidal formulation according to claim 1 comprising a compound of formula I(a) and a compound of formula II(a), said compound of formula I(a) and said compound of formula II(a) being present in the ratio range of 5:1 to 1:250 by weight.
3. A fungicidal formulation according to claim 1 comprising a compound of formula I(a) and a compound of formula II(b), said compound of formula I(a) and said compound of formula II(b) being present in the ratio range of 5:1 to 1:250 by weight.
4. A fungicidal formulation according to claim 1 comprising a compound of formula I(b) and a compound of formula II(a), said compound of formula I(b) and said compound of formula II(a) being present in the ratio range of 5:1 to 1:250 by weight.
5. A fungicidal formulation according to claim 1 comprising a compound of formula I(b) and a compound of formula II(b), said compound of formula I(b) and said compound of formula II(b) being present in the ratio range of 5:1 to 1:250 by weight.
6. A method of treating fungal infections of plants which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as claimed in claim 1.
7. A method according to claim 7 which comprises applying the formulation to grapes.
8. A method according to claim 6 in which the fungicidal formation is applied as a foliar spray, said compound of formula I(a) being used at an application rate of from 10 to 500 grams per hectare, amd said compound of formula I(b) being used at an application rate of from 10 to 100 grams per hectare.
9. A method according to claim 8 in which the compound of formula II(a) is applied at a rate of from 100 to 2,500 g per hectare, and in which the compound of formula II(b) is applied or a rate of from 50 to 500 g per hectare.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1282478 | 1978-04-01 | ||
| GB12824/78 | 1978-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1128854A true CA1128854A (en) | 1982-08-03 |
Family
ID=10011816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA324,339A Expired CA1128854A (en) | 1978-04-01 | 1979-03-28 | Fungicidal formulations |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS54132233A (en) |
| AR (4) | AR225414A1 (en) |
| AT (1) | AT364196B (en) |
| AU (1) | AU527924B2 (en) |
| BE (1) | BE875198A (en) |
| BG (4) | BG31469A3 (en) |
| BR (1) | BR7901929A (en) |
| CA (1) | CA1128854A (en) |
| CH (1) | CH638079A5 (en) |
| CS (4) | CS217978B2 (en) |
| DD (1) | DD143552A5 (en) |
| DE (1) | DE2912491A1 (en) |
| DK (4) | DK126779A (en) |
| EG (1) | EG13864A (en) |
| ES (1) | ES479135A1 (en) |
| FR (4) | FR2422332A1 (en) |
| GB (1) | GB2077591B (en) |
| GR (1) | GR67710B (en) |
| HU (2) | HU182518B (en) |
| IE (1) | IE47941B1 (en) |
| IL (1) | IL56963A (en) |
| IN (1) | IN149760B (en) |
| IT (1) | IT1120402B (en) |
| LU (1) | LU81096A1 (en) |
| NL (1) | NL7902435A (en) |
| NO (4) | NO147202C (en) |
| NZ (1) | NZ190062A (en) |
| PL (4) | PL122824B1 (en) |
| PT (1) | PT69407A (en) |
| RO (2) | RO80251A (en) |
| SE (4) | SE446811B (en) |
| SU (1) | SU1311600A3 (en) |
| TR (1) | TR20289A (en) |
| ZA (1) | ZA791494B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS217978B2 (en) | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
| DE3326664A1 (en) * | 1982-07-29 | 1984-02-02 | Lilly Industries Ltd., London | Fungicidal agent and process for its preparation |
| EP0645084B1 (en) * | 1993-09-24 | 1996-07-31 | BASF Aktiengesellschaft | Fungicidal mixtures |
| PL224139B1 (en) | 2014-08-01 | 2016-11-30 | Ekobenz Spółka Z Ograniczoną Odpowiedzialnością | Fuel blend, particularly for engines with spark ignition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
| OA04979A (en) * | 1974-04-09 | 1980-11-30 | Ciba Geigy | New aniline derivatives useful as microbicidal agents and their preparation process. |
| GB1561634A (en) * | 1975-10-29 | 1980-02-27 | Lilly Industries Ltd | Fungicidal compositions |
| DE2560510C2 (en) * | 1975-11-26 | 1989-02-16 | Bayer Ag, 5090 Leverkusen, De | |
| GB1559820A (en) * | 1975-12-09 | 1980-01-30 | Lilly Industries Ltd | Fungicidal compositions |
| GB1581527A (en) * | 1976-08-18 | 1980-12-17 | Lilly Industries Ltd | Fungicidal formulations |
| CS217978B2 (en) | 1978-04-01 | 1983-02-25 | Lilly Industries Ltd | Fungicide means |
-
1979
- 1979-03-23 CS CS802271A patent/CS217978B2/en unknown
- 1979-03-23 CS CS802269A patent/CS217976B2/en unknown
- 1979-03-23 CS CS802270A patent/CS217977B2/en unknown
- 1979-03-28 EG EG190/79A patent/EG13864A/en active
- 1979-03-28 FR FR7907805A patent/FR2422332A1/en active Granted
- 1979-03-28 SE SE7902780A patent/SE446811B/en not_active IP Right Cessation
- 1979-03-28 AR AR275965A patent/AR225414A1/en active
- 1979-03-28 CA CA324,339A patent/CA1128854A/en not_active Expired
- 1979-03-28 IL IL56963A patent/IL56963A/en unknown
- 1979-03-28 AU AU45485/79A patent/AU527924B2/en not_active Ceased
- 1979-03-28 DK DK126779A patent/DK126779A/en not_active Application Discontinuation
- 1979-03-28 GR GR58713A patent/GR67710B/el unknown
- 1979-03-29 IN IN307/CAL/79A patent/IN149760B/en unknown
- 1979-03-29 TR TR20289A patent/TR20289A/en unknown
- 1979-03-29 BG BG045202A patent/BG31469A3/en unknown
- 1979-03-29 NL NL7902435A patent/NL7902435A/en not_active Application Discontinuation
- 1979-03-29 CH CH290179A patent/CH638079A5/en not_active IP Right Cessation
- 1979-03-29 LU LU81096A patent/LU81096A1/en unknown
- 1979-03-29 BE BE6/46792A patent/BE875198A/en not_active IP Right Cessation
- 1979-03-29 ZA ZA791494A patent/ZA791494B/en unknown
- 1979-03-29 PT PT69407A patent/PT69407A/en unknown
- 1979-03-29 CS CS792108A patent/CS221251B2/en unknown
- 1979-03-29 BR BR7901929A patent/BR7901929A/en unknown
- 1979-03-29 BG BG043056A patent/BG31364A3/en unknown
- 1979-03-29 BG BG045204A patent/BG31471A3/en unknown
- 1979-03-29 BG BG045203A patent/BG31470A3/en unknown
- 1979-03-29 DE DE19792912491 patent/DE2912491A1/en not_active Ceased
- 1979-03-29 JP JP3768479A patent/JPS54132233A/en active Pending
- 1979-03-30 IT IT48541/79A patent/IT1120402B/en active
- 1979-03-30 DD DD79211922A patent/DD143552A5/en unknown
- 1979-03-30 NZ NZ190062A patent/NZ190062A/en unknown
- 1979-03-30 RO RO79102292A patent/RO80251A/en unknown
- 1979-03-30 HU HU79LI338A patent/HU182518B/en unknown
- 1979-03-30 AT AT0239679A patent/AT364196B/en not_active IP Right Cessation
- 1979-03-30 HU HU83114A patent/HU189633B/en unknown
- 1979-03-30 SU SU792748355A patent/SU1311600A3/en active
- 1979-03-30 GB GB8112001A patent/GB2077591B/en not_active Expired
- 1979-03-30 RO RO7997081A patent/RO75492A/en unknown
- 1979-03-30 ES ES479135A patent/ES479135A1/en not_active Expired
- 1979-03-30 NO NO791074A patent/NO147202C/en unknown
- 1979-03-31 PL PL1979230914A patent/PL122824B1/en unknown
- 1979-03-31 PL PL1979230915A patent/PL123456B1/en unknown
- 1979-03-31 PL PL1979214575A patent/PL119526B1/en unknown
- 1979-03-31 PL PL1979230916A patent/PL122819B1/en unknown
- 1979-06-29 FR FR7916982A patent/FR2424701A1/en active Granted
- 1979-06-29 FR FR7916985A patent/FR2424702A1/en active Granted
- 1979-06-29 FR FR7916986A patent/FR2424703A1/en active Granted
- 1979-08-08 IE IE665/79A patent/IE47941B1/en unknown
-
1981
- 1981-08-06 AR AR286356A patent/AR227933A1/en active
- 1981-08-06 AR AR286355A patent/AR227932A1/en active
- 1981-08-06 AR AR286354A patent/AR228962A1/en active
-
1982
- 1982-06-30 NO NO822278A patent/NO148768C/en unknown
- 1982-06-30 NO NO822279A patent/NO148767C/en unknown
- 1982-06-30 NO NO822277A patent/NO148766C/en unknown
-
1984
- 1984-02-22 SE SE8400978A patent/SE8400978D0/en not_active Application Discontinuation
- 1984-02-22 SE SE8400976A patent/SE454399B/en not_active IP Right Cessation
- 1984-02-22 SE SE8400977A patent/SE8400977D0/en not_active Application Discontinuation
-
1988
- 1988-03-04 DK DK120788A patent/DK120788A/en unknown
- 1988-03-04 DK DK120588A patent/DK120588D0/en not_active Application Discontinuation
- 1988-03-04 DK DK120688A patent/DK120688A/en not_active Application Discontinuation
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